Synfacts 2011(4): 0375-0375  
DOI: 10.1055/s-0030-1259675
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Sonogashira-Heteroannulative Route to Dihydroisobenzofurans

Contributor(s): Victor Snieckus, Yigang Zhao
M. Dell’Acqua, D. Facoetti, G. Abbiati*, E. Rossi
Universita degli Studi di Milano, Italy
Further Information

Publication History

Publication Date:
18 March 2011 (online)

Significance

Reported is a synthesis of dihydroisobenzofurans via a Sonogashira-hetero­annulation strategy. 2-Bromoaryl and 3-pyridyl ­aldehydes, terminal alkynes and methanol are employed in this one-pot, microwave-assisted process under palladium and copper catalysis to afford dihydroisobenzofurans in good to excellent yields. The Sonogashira cross-coupling is followed by t-BuOK-generated methoxide annulations, which may also involve metal catalysis. The scope of substituents on the aromatic was not well investigated.